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More Impressive Is The Successful Founder Who Took The Road Less Traveled

An amazing story is going around right now about a high school senior who has been accepted to Harvard. What’s more notable is that she was basically from little means in high school and even homeless for her entire senior year. Even more admirable is how she tried to live a normal life despite her situation, playing sports and partaking in extracurricular activities right along with her peers.

Dawn grew up in a ramshackle home with no electricity and no running water. She often went days, even weeks without showering. She and her brother Shane — who was equally studious in his schoolwork — would walk 20 minutes to a public park to fetch water.

“We would get water jugs and fill them up at the park, using the spigots in the bathroom. And we would use that to flush the toilet or cook with. Stuff like that,” she says.

She confided in a staff member at school. She had trouble doing homework at nighttime because her home had no electricity and she couldn’t afford candles. It was difficult to read in the dark.

Obviously Dawn is not a startup founder, but I think about stuff like this a lot since I am going through something similar. Do I have it as bad as Dawn? No, for sure not. But am I sacrificing a lot and going through hardships to see my dream come true? Yes, for damn sure.

It’s funny, the naiveté one has when starting a company can be their best friend because if they knew how hard it would be or what it actually takes to succeed, they probably wouldn’t even start. Especially for the one’s who aren’t cut from the same mold as others they are competing against.

The Well Worn Path Of Tech Founders

A kid grows up playing with computers and rather than playing sports, and he focused on writing the most code he possibly could rather than getting the most girls he possible could. Other students view him as an outcast or a nerd. He goes to college, usually Stanford or MIT or some other prestigious school and studies engineering or Computer Science. Once he graduates he usually receives employment offers from Google, Microsoft, Facebook or other large and successful technology companies. And now he wants to start a company. On paper he’s a prime candidate to be successful.

Unknown to most first time founders is how much this well worn path is valued. It’s cred. It’s validation. “He worked at Google so he knows how to build a company” investors, bloggers and others assume. Money is easier to come by when you take the well worn path. Attracting engineering talent is not as big of deal if you have the ‘generally accepted credentials’. People just assume you and your company will be a success.

But is that really true?

Google can help an engineer polish their skills and become one of the best in the wold at their trade. But what does Google teach an engineer about building a company? Or Microsoft? I’m no expert but BIG corporations are about the farthest thing from scrappy, early stage startups.

I am more impressed with successful founders who took the road less traveled. The ones who didn’t go to Stanford. The ones who might not have a solid network of investors and engineers right out of the gate but work like hell and take 50 coffee meetings each year just to get to know other entrepreneurs. The ones who work 2x as hard and 2x as smart as others to get to where they are now.

I love the person who looks impossible in the eye and basically says “f-you, i’m doing it anyway!” The person who changes paths mid-journey because he knows the one he’s on is too worn down from all the others who preceded him.

Impressive is the one who cuts his own path.

And isn’t that what an entrepreneur actually does? They shrewdly navigate the business ecosystem to give themselves the greatest advantage possible with the least amount of resources and against all odds. Most impressive to me are the ones who started the lowest and finished the highest.

The Road Not Taken

Robert Frost

Two roads diverged in a yellow wood,
And sorry I could not travel both
And be one traveler, long I stood
And looked down one as far as I could
To where it bent in the undergrowth;

Then took the other, as just as fair,
And having perhaps the better claim
Because it was grassy and wanted wear,
Though as for that the passing there
Had worn them really about the same,

And both that morning equally lay
In leaves no step had trodden black.
Oh, I marked the first for another day!
Yet knowing how way leads on to way
I doubted if I should ever come back.

I shall be telling this with a sigh
Somewhere ages and ages hence:
Two roads diverged in a wood, and I,
I took the one less traveled by,
And that has made all the difference.

One thought on “More Impressive Is The Successful Founder Who Took The Road Less Traveled”

I don’t have a tech company, but I have definitely been one of those scrappy ones down the road less traveled. I think that what separates us from those who go down the worn paths is that they wait for permission to go out and succeed. We other ones just go out and make the way to do it. In fact, many of us were denied permission, but we did it anyway. “We will either find a way, or make one.” Hannibal.